(2R)-1-O-acetyl-2-O-(β-D-glucopyranosyl)glycerol | 158110-30-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2R)-1-O-acetyl-2-O-(β-D-glucopyranosyl)glycerol
• 英文别名: 1-O-acetyl-2-O-β-D-glucopyranosyl-sn-glycerol；lilioside A；[(2R)-3-hydroxy-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] acetate
• CAS: 158110-30-6
• 化学式: C₁₁H₂₀O₉
• 分子量: 296.274
• InChiKey: WOXRFOGJAFXBAH-MPVQUNCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R)-1-O-acetyl-2-O-(β-D-glucopyranosyl)glycerol 、 4-溴苯甲酰氯 在 吡啶 作用下， 以33 mg的产率得到lilioside A penta-p-bromobenzoate
  参考文献：
  名称：

  Lilioside a from Lilium longiflorum: Synthesis and absolute configuration

  摘要：

  DOI：

  10.1016/0031-9422(90)85276-l
• 作为产物：
  描述：

  laminaribiose 在 钯 吡啶 、 lead(IV) acetate 、 sodium tetrahydroborate 、 氢气 、 sodium hydride 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 16.0h， 生成 (2R)-1-O-acetyl-2-O-(β-D-glucopyranosyl)glycerol
  参考文献：
  名称：

  Lilioside a from Lilium longiflorum: Synthesis and absolute configuration

  摘要：

  DOI：

  10.1016/0031-9422(90)85276-l

文献信息

• 1H NMR acetyl methyl resonances of peracetylated lilioside B: a tool for the stereochemical identification of its partially acetylated derivatives
  作者：Diego Colombo、Franca Marinone Albini、Antonio Scala、Ida M. Taino、Lucio Toma

  DOI：10.1016/s0957-4166(00)86274-6

  日期：1994.10

  Through C-13-H-1 heteronuclear shift correlation experiments all the acetyl methyl resonances of 1,3-di-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)glycerol and of the diastereoisomeric (2R) and (2S)-1-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)glycerol have been assigned in the 1H NMR spectra; partially acetylated derivatives of 2-O-(beta-D-glucopyranosyl)glycerol, Iilioside B, can so be easily identified and their configuration established also when mixtures of several derivatives are under investigation.
• Regio- and diastereoselective lipase-catalyzed preparation of acetylated 2-O-glucosylglycerols
  作者：Diego Colombo、Fiamma Rondietti、Antonio Scala、Ida M. Taino、Pranca Marinone Albini、Lucio Toma

  DOI：10.1016/0957-4166(94)80181-9

  日期：1994.7

  2-O-(beta-D-Glucopyranosyl) glycerol and 2-O-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)glycerol have been submitted to lipase-catalyzed acetylation using Pseudomonas cepacia (LPS) and Candida antarctica (LCA) lipases in organic solvent. The reactions involved the glycerol moiety and were highly diastereoselective: LPS yielded the (2S)-1-O-acetylderivative, while, more interestingly, LCA yielded the (2R)-1-O-acetyl-derivative; in this way the natural compound lilioside A could be obtained. Conversely, lipase-catalyzed hydrolysis of the fully acetylated 1,3-di-O-acetyl-2-O-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)glycerol using LCA furnished the (2S)-1-O-acetyl-derivative showing the same steric preference as the reverse reaction.
• KANEDA, MIYUKI, PHYTOCHEMISTRY, 29,(1990) N1, C. 3559-3564
  作者：KANEDA, MIYUKI

  DOI：——

  日期：——